JP6519592B2 - ピリダジン化合物 - Google Patents
ピリダジン化合物 Download PDFInfo
- Publication number
- JP6519592B2 JP6519592B2 JP2016552036A JP2016552036A JP6519592B2 JP 6519592 B2 JP6519592 B2 JP 6519592B2 JP 2016552036 A JP2016552036 A JP 2016552036A JP 2016552036 A JP2016552036 A JP 2016552036A JP 6519592 B2 JP6519592 B2 JP 6519592B2
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- JP
- Japan
- Prior art keywords
- group
- alkyl
- compound
- halogen atoms
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000004892 pyridazines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 447
- 125000005843 halogen group Chemical group 0.000 claims description 212
- -1 pyridazine compound Chemical class 0.000 claims description 148
- 239000000203 mixture Substances 0.000 claims description 145
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 142
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 91
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 69
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 57
- 125000004429 atom Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001153 fluoro group Chemical group F* 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 241000238421 Arthropoda Species 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 230000001473 noxious effect Effects 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 133
- 229910052739 hydrogen Inorganic materials 0.000 description 123
- 238000004519 manufacturing process Methods 0.000 description 104
- 238000005160 1H NMR spectroscopy Methods 0.000 description 78
- 239000000543 intermediate Substances 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- 239000000243 solution Substances 0.000 description 65
- 150000001204 N-oxides Chemical class 0.000 description 57
- 239000012044 organic layer Substances 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 47
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000009472 formulation Methods 0.000 description 41
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- 239000002585 base Substances 0.000 description 36
- 241000238631 Hexapoda Species 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 34
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
- 229910052731 fluorine Inorganic materials 0.000 description 33
- 238000012360 testing method Methods 0.000 description 32
- 238000010898 silica gel chromatography Methods 0.000 description 30
- 239000012085 test solution Substances 0.000 description 29
- 238000001816 cooling Methods 0.000 description 28
- 229910052801 chlorine Inorganic materials 0.000 description 27
- 125000001309 chloro group Chemical group Cl* 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000007800 oxidant agent Substances 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 241000607479 Yersinia pestis Species 0.000 description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 14
- 241000256602 Isoptera Species 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 244000045947 parasite Species 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 241000238876 Acari Species 0.000 description 11
- 241001600408 Aphis gossypii Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 241001124076 Aphididae Species 0.000 description 9
- 240000008067 Cucumis sativus Species 0.000 description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 9
- 235000019345 sodium thiosulphate Nutrition 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 7
- 241000239290 Araneae Species 0.000 description 7
- 241000254173 Coleoptera Species 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 241001414989 Thysanoptera Species 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 235000010265 sodium sulphite Nutrition 0.000 description 7
- 241001498622 Cixius wagneri Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- 241000257159 Musca domestica Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 6
- 150000008041 alkali metal carbonates Chemical class 0.000 description 6
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 6
- 150000008046 alkali metal hydrides Chemical class 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- 230000008034 disappearance Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 230000011890 leaf development Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 241000500437 Plutella xylostella Species 0.000 description 5
- 241000255588 Tephritidae Species 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241001124134 Chrysomelidae Species 0.000 description 4
- 241001517923 Douglasiidae Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241001556089 Nilaparvata lugens Species 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 241001466030 Psylloidea Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 239000003915 liquefied petroleum gas Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 231100000614 poison Toxicity 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 3
- KJGYBFLEIPDFNQ-UHFFFAOYSA-N 2,2,2-trifluoroethyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KJGYBFLEIPDFNQ-UHFFFAOYSA-N 0.000 description 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 C*(*)c(c(*)c(*)c(*)c1*c2c3*)c1-c2nnc3O* Chemical compound C*(*)c(c(*)c(*)c(*)c1*c2c3*)c1-c2nnc3O* 0.000 description 3
- 241001529599 Colaspis brunnea Species 0.000 description 3
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- 241000196324 Embryophyta Species 0.000 description 3
- 241000086608 Empoasca vitis Species 0.000 description 3
- 241000258937 Hemiptera Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 241001671709 Nezara viridula Species 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
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- 241001516578 Phylloxera notabilis Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000254152 Sitophilus oryzae Species 0.000 description 3
- 241000322273 Stenolophus lecontei Species 0.000 description 3
- 241000511627 Tipula paludosa Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910001502 inorganic halide Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 3
- 239000004544 spot-on Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
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- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
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- Health & Medical Sciences (AREA)
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JP2014204515 | 2014-10-03 | ||
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PCT/JP2015/077420 WO2016052455A1 (ja) | 2014-10-03 | 2015-09-29 | ピリダジン化合物 |
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US (1) | US9924719B2 (pt) |
EP (1) | EP3202761B1 (pt) |
JP (1) | JP6519592B2 (pt) |
CN (1) | CN107074779B (pt) |
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JPWO2017065228A1 (ja) * | 2015-10-16 | 2018-08-02 | 住友化学株式会社 | ピラジン化合物及びその有害節足動物防除剤 |
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BR112018008306B1 (pt) * | 2015-11-02 | 2022-06-14 | Sumitomo Chemical Company, Limited | Composto de pirimidina, composição para o controle de um artrópode nocivo e método para o controle de um artrópode nocivo |
JP2017075161A (ja) * | 2015-11-26 | 2017-04-20 | 住友化学株式会社 | 有害生物防除組成物およびその用途 |
WO2017150209A1 (ja) * | 2016-02-29 | 2017-09-08 | 住友化学株式会社 | 複素環化合物 |
JP6801245B2 (ja) * | 2016-06-14 | 2020-12-16 | Dic株式会社 | 液晶化合物の製造方法及びその化合物 |
CN109415318B (zh) * | 2016-07-07 | 2022-06-28 | 住友化学株式会社 | 杂环化合物及含有其的有害节肢动物防治剂 |
EP3549933B1 (en) * | 2016-12-01 | 2022-02-16 | Sumitomo Chemical Company, Limited | Heterocyclic compound, and arthropod pest control composition containing same |
JP7013213B2 (ja) * | 2017-05-26 | 2022-01-31 | 日本化薬株式会社 | ピラジン化合物 |
WO2018221720A1 (ja) | 2017-06-01 | 2018-12-06 | 住友化学株式会社 | 複素環化合物及びそれを含有する組成物 |
KR101904675B1 (ko) | 2017-12-15 | 2018-10-04 | 씨제이제일제당 (주) | 5'-이노신산을 생산하는 미생물 및 이를 이용한 5'-이노신산의 생산 방법 |
US11180754B2 (en) | 2017-12-15 | 2021-11-23 | Cj Cheiljedang Corporation | Polypeptide and method of producing IMP using the same |
KR101916611B1 (ko) | 2017-12-15 | 2018-11-07 | 씨제이제일제당 (주) | 신규 폴리펩타이드 및 이를 이용한 imp 생산방법 |
BR112020012168B1 (pt) | 2017-12-22 | 2024-01-23 | Sumitomo Chemical Company, Limited | Composto heterocíclico e composição para controlar um artrópode nocivo |
KR101916622B1 (ko) | 2018-01-04 | 2018-11-07 | 씨제이제일제당 (주) | 신규 폴리펩타이드 및 이를 이용한 imp 생산방법 |
AR115495A1 (es) | 2018-06-06 | 2021-01-27 | Syngenta Crop Protection Ag | Derivados heterocíclicos con sustituyentes que contienen azufre activos como plaguicidas |
US20220135537A1 (en) * | 2019-02-20 | 2022-05-05 | Sumitomo Chemical Company, Limited | Ether compound and harmful arthropod-controlling composition containing same |
WO2024189139A1 (en) | 2023-03-14 | 2024-09-19 | Syngenta Crop Protection Ag | Control of pests resistant to insecticides |
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JPS591469A (ja) * | 1982-06-17 | 1984-01-06 | Nippon Soda Co Ltd | ピリダジン誘導体及び選択的除草剤 |
KR20010014410A (ko) * | 1997-07-01 | 2001-02-26 | 미우라 아끼라 | 3-치환된 페닐-4-할로피리다진 유도체, 이를 유효성분으로 하는 농약 및 이의 중간체 |
JPH1192456A (ja) * | 1997-07-01 | 1999-04-06 | Mitsubishi Chemical Corp | 新規3−置換フェニル−4−ハロピリダジン誘導体、ならびにこれを有効成分とする農薬およびこの中間体 |
JP2001039954A (ja) | 1999-05-24 | 2001-02-13 | Tomono Agrica Co Ltd | ヘテロ環誘導体 |
JP2003313169A (ja) | 2002-04-19 | 2003-11-06 | Otsuka Chemical Holdings Co Ltd | 4,4−ジフルオロ−3−ブテニル化合物及び農園芸用殺虫・殺ダニ剤 |
JP2013060420A (ja) * | 2011-08-23 | 2013-04-04 | Ishihara Sangyo Kaisha Ltd | 有害生物防除剤 |
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- 2015-09-29 CN CN201580053557.4A patent/CN107074779B/zh active Active
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Cited By (1)
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JPWO2017065228A1 (ja) * | 2015-10-16 | 2018-08-02 | 住友化学株式会社 | ピラジン化合物及びその有害節足動物防除剤 |
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BR112017006428A2 (pt) | 2017-12-12 |
WO2016052455A1 (ja) | 2016-04-07 |
EP3202761A4 (en) | 2018-05-30 |
CN107074779A (zh) | 2017-08-18 |
EP3202761A1 (en) | 2017-08-09 |
EP3202761B1 (en) | 2022-03-16 |
US9924719B2 (en) | 2018-03-27 |
US20170295787A1 (en) | 2017-10-19 |
CN107074779B (zh) | 2020-05-01 |
JPWO2016052455A1 (ja) | 2017-07-20 |
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